Your First Engineering Hire Will Make or Break You
Why your first engineering hire matters more than your next funding round
You posted a job ad for a senior full-stack developer. Within days, 400 applications landed in your inbox. You spent a weekend reading CVs and you still cannot tell who is good.
That is normal.
Hiring engineers is hard even for experienced CTOs. For a founder doing it the first time, it feels like guesswork. Most founders get this hire wrong. Not because they are poor judges of character, but because they focus on surface signals.
The job description reads like a checklist. Five years of React and TypeScript. PostgreSQL. AWS. Docker. The result is predictable. You either hire someone who matches keywords but struggles in a messy, early product. Or you hire someone familiar who is “good with code” and hope it works out.
Your first engineer is not filling a gap. They are shaping how your company builds software. The patterns they introduce will be copied. The shortcuts they take will become normal. The way they structure code, handle data, manage errors and deploy changes will define the baseline for everyone who joins after them.
That is why “senior full-stack developer” is often the wrong framing. It describes tools. What you actually need is someone who can own the product and make decisions in uncertainty.
I tend to think about engineers in two broad groups. Builders and Optimisers.
Optimisers improve existing systems. They refactor, improve performance, tighten processes. They are strong when there is already structure.
Builders create structure where none exists. They are comfortable with ambiguity. They make decisions with incomplete information. They ship something that works, then improve it. They do not wait for perfect requirements.
At an early stage, you usually need a builder.
Especially if your current codebase was done quickly, possibly with AI tools. You need someone who can step into that reality, understand the intent, and improve it without expecting it to be clean. If you are not technical, you can still evaluate this.
Stop focusing on technologies. Start focusing on decisions.
Ask candidates to walk you through a real trade-off they made.
What were the options. What did they choose. Why.
Ask about a project where requirements changed halfway through. What broke. What did they adjust. What would they do differently now.
You are not testing whether they know React. You are testing how they think, how they handle ambiguity, and whether they take ownership.
Listen carefully to how they describe past work. Do they talk about trade-offs. Do they explain constraints. Can they point to decisions they personally made and the consequences of those decisions.
Ownership matters more than elegance at this stage.
On compensation, this is not the place to optimise for cost. You are asking someone to take responsibility for your entire technical foundation. Paying below market usually means you attract someone who is not yet ready for that responsibility. That becomes expensive later.
Set clear expectations for the first 90 days.
By the end of week one, they should be able to run the system locally and deploy a small change.
By the end of month one, they should understand the architecture well enough to explain it clearly.
By month three, they should ship independently and start challenging parts of the system that need improvement.
If after 90 days you are still the only person who truly understands how things work, the hire is not doing what you need. If after 90 days they are raising the bar and pushing the product forward, you hired well.
Do not rush this because you feel behind. A weak first engineering hire sets you back further than a slow, deliberate search.
I help founders design their first engineering hire. If you are about to post that job ad, it might be worth a conversation first. Book a free 20-min call